Hydrogen Peroxide → HCID 10184406, compound

Participants

Reaction Steps

3-{7-(Cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}benzonitrile (45 mg, 0.097 mmol) was dissolved in hot methanol (2 mL). Subsequently, the solution was cooled down to room temperature and 30% ammonium hydroxide (2 mL) was added. The reaction mixture was then cooled to 0° C., and 30% hydrogen peroxide was added. After stirring at room temperature for 8 hours, water was added and the resulting mixture extracted with ethyl acetate. The organics were dried over magnesium sulfate. Filtration and concentration, followed by purification with flash chromatography (95:5 dichloromethane:methanol), gave 3-{7-(cyclopentylamino)-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}benzamide (18 mg, 39% yield) as a yellow solid. 1H NMR (CDCl3): δ 8.12 (s, 1H), 7.99 (d, 1H), 7.92 (d, 1H), 7.79 (d, 1H), 7.70 (d, 1H), 7.51 (t, 1H), 7.32 (t, 1H), 6.28 (d, 1H), 6.18 (broad, 1H), 6.05 (d, 1H), 6.02 (d, 1H), 5.82 (broad, 1H), 5.25 (d, 1H), 4.30 (m, 1H), 4.00 (m, 1H), 2.15 (m, 2H), 2.03 (m, 2H), 1.81–1.50 (m, 12H). MS m/z 482 (M+1).

Provenance & Evidence